(2E,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2-pentenal

Base Information

Chemical Name:(2E,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2-pentenal
CAS No.:863222-42-8
Molecular Formula:C₃₆H₅₀O₆Si
Molecular Weight:606.875
Hs Code.:

(2E,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2-pentenal

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Chemical Property of (2E,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2-pentenal

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Technology Process of (2E,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2-pentenal

There total 12 articles about (2E,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2-pentenal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: tert-Butyl-dimethyl-((Z)-(2R,4aR,6S,7R,11aS)-2-phenyl-6-vinyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-yloxy)-silane

: 863222-42-8
(2E,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2-pentenal

Guidance literature:: Multi-step reaction with 9 steps

1: 113.5 mg / 1,2-ethanedithiol; NaHCL₃; Zn(OTf)2 / CH₂Cl₂ / 2.5 h / 0 °C

2: NaH; TBAI / tetrahydrofuran / 15 h / 24 °C

3: 135.8 mg / TBAF / tetrahydrofuran / 18 h / 25 °C

4: 90 percent / PMe₃ / CH₂Cl₂ / 1 h / 24 °C

5: 99 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

6: 76 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 24 °C

7: 79 percent / Me₃Al / benzene; hexane / 1 h / 24 °C

8: 55 percent / Bu₃SnH; BF₃*Et₂O / CH₂Cl₂ / 0.25 h / -18 °C

9: 100 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; trimethylaluminum; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; ethane-1,2-dithiol; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; benzene; 4: hetero-Michael addition;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 100-39-0
benzyl bromide

: 863222-42-8
(2E,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2-pentenal

Guidance literature:: Multi-step reaction with 8 steps

1: NaH; TBAI / tetrahydrofuran / 15 h / 24 °C

2: 135.8 mg / TBAF / tetrahydrofuran / 18 h / 25 °C

3: 90 percent / PMe₃ / CH₂Cl₂ / 1 h / 24 °C

4: 99 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

5: 76 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 24 °C

6: 79 percent / Me₃Al / benzene; hexane / 1 h / 24 °C

7: 55 percent / Bu₃SnH; BF₃*Et₂O / CH₂Cl₂ / 0.25 h / -18 °C

8: 100 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; trimethylaluminum; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; benzene; 3: hetero-Michael addition;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 475641-59-9
(Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene

: 863222-42-8
(2E,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2-pentenal

Guidance literature:: Multi-step reaction with 12 steps

1.1: 24 percent / TFA; H₂O / tetrahydrofuran / 4 h / 0 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -20 °C

3.1: NaHMDS / tetrahydrofuran / 1 h / 24 °C

3.2: tetrahydrofuran / 2.5 h / -78 °C

4.1: 113.5 mg / 1,2-ethanedithiol; NaHCL₃; Zn(OTf)2 / CH₂Cl₂ / 2.5 h / 0 °C

5.1: NaH; TBAI / tetrahydrofuran / 15 h / 24 °C

6.1: 135.8 mg / TBAF / tetrahydrofuran / 18 h / 25 °C

7.1: 90 percent / PMe₃ / CH₂Cl₂ / 1 h / 24 °C

8.1: 99 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

9.1: 76 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 24 °C

10.1: 79 percent / Me₃Al / benzene; hexane / 1 h / 24 °C

11.1: 55 percent / Bu₃SnH; BF₃*Et₂O / CH₂Cl₂ / 0.25 h / -18 °C

12.1: 100 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; trimethylaluminum; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; ethane-1,2-dithiol; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; benzene; 2.1: Swern oxidation / 3.2: Wittig reaction / 7.1: hetero-Michael addition;
DOI:10.1016/j.tet.2005.05.073